Which airlines fly to Chicago?

Air Canada, United Airlines and Porter Airlines are the top three most popular airlines that fly to Chicago from Region of Ontario according to our data. Air Canada is the first choice among our users, with 56% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How long does it take to fly to Chicago?

Flight times from Region of Ontario to Chicago vary, but if you’re flying out of Ottawa and flying into Chicago O'Hare Intl Airport (one of the most popular routes), then the duration is 2h 20m on average. Another popular route from Region of Ontario to Chicago is flying from Toronto to Chicago O'Hare Intl Airport, which will take roughly 5h 08m. Keep in mind that layovers or delays could extend your travel time.

How many flights depart from Region of Ontario to Chicago on average per day?

88 flights are operational daily from Region of Ontario to Chicago as of February 2026. The most popular departure time for this route is 6:00a.m., with 49% of flights per day taking off at noon.

How many flights depart from Region of Ontario to Chicago on average per week?

616 flights are operational weekly from Region of Ontario to Chicago as of February 2026. The most popular departure day for this route is Fri, with 16% of flights per week taking off on this day.

What is the cheapest airline that flies from Ontario to Chicago?

United Airlines, Air Canada, and Porter Airlines are the most popular carriers operating from Ontario to Chicago

When did momondo last update prices for flights from Ontario to Chicago?

Prices for flights from Ontario to Chicago were last updated today.

How many operators does momondo search for flights from Ontario to Chicago?

There are 5 operators available for flights from Ontario to Chicago as of February 2026.

How old do you have to be to fly from Ontario to Chicago?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Ontario to Chicago.

What documentation or ID do you need to fly to Chicago?

The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

C$ 157 Cheap Flights from Ontario to Chicago in 2026

1 adult

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Find the cheapest flights from Ontario to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:50 a.m. - 10:05 a.m.

YUL

MDW

4h 15m

1 stop

11:00 a.m. - 5:45 p.m.

MDW

YUL

5h 45m

1 stop

C$ 228Porter Airlines

Thu, 19 Mar - Thu, 26 Mar

6:50 a.m. - 10:15 a.m.

YUL

MDW

4h 25m

1 stop

10:25 a.m. - 6:15 p.m.

MDW

YUL

6h 50m

1 stop

C$ 230Porter Airlines

Tue, 28 Apr - Mon, 4 May

9:25 a.m. - 11:18 a.m.

YUL

ORD

2h 53mdirect

3:35 p.m. - 6:40 p.m.

ORD

YUL

2h 05mdirect

C$ 241Air Canada

Thu, 19 Mar - Mon, 23 Mar

9:25 a.m. - 11:18 a.m.

YUL

ORD

2h 53mdirect

8:40 a.m. - 11:51 a.m.

ORD

YUL

2h 11mdirect

C$ 242Air Canada

Thu, 26 Mar - Mon, 30 Mar

9:15 a.m. - 10:05 a.m.

YTZ

MDW

1h 50mdirect

11:00 a.m. - 1:42 p.m.

MDW

YTZ

1h 42mdirect

C$ 264Multiple Airlines

Thu, 19 Mar - Thu, 26 Mar

6:00 a.m. - 8:00 a.m.

YUL

ORD

3h 00mdirect

6:00 a.m. - 3:16 p.m.

ORD

YUL

8h 16m

1 stop

C$ 265United Airlines

Tue, 17 Mar - Sun, 22 Mar

11:00 a.m. - 11:50 a.m.

YTZ

MDW

1h 50mdirect

12:35 p.m. - 3:17 p.m.

MDW

YTZ

1h 42mdirect

C$ 267Multiple Airlines

Sat, 4 Apr - Sat, 11 Apr

8:50 a.m. - 9:50 a.m.

YYZ

ORD

2h 00mdirect

9:20 p.m. - 11:59 p.m.

ORD

YYZ

1h 39mdirect

C$ 269Lufthansa

Sat, 4 Apr - Mon, 6 Apr

9:45 a.m. - 11:37 a.m.

YUL

ORD

2h 52mdirect

7:13 a.m. - 10:40 a.m.

ORD

YUL

2h 27mdirect

C$ 271Lufthansa

Sat, 4 Apr - Mon, 20 Apr

7:00 a.m. - 8:03 a.m.

YYZ

ORD

2h 03mdirect

8:45 a.m. - 2:19 p.m.

ORD

YYZ

4h 34m

1 stop

C$ 274United Airlines

Fri, 10 Apr - Sun, 12 Apr

American Airlines flights from Region of Ontario to Chicago

Our best American Airlines deals on Region of Ontario to Chicago flight tickets

American Airlines

18 Mar

YYZ1:10 p.m.Toronto Pearson Intl

2h 00m

ORD2:10 p.m.Chicago O'Hare Intl

25 Mar

ORD5:00 a.m.Chicago O'Hare Intl

5h 13m

1 stop

YYZ11:13 a.m.Toronto Pearson Intl

C$ 275

American Airlines

10 Apr

YUL4:16 p.m.Montreal Pierre Elliott Trudeau Intl

16h 23m

1 stop

ORD7:39 a.m.Chicago O'Hare Intl

19 Apr

ORD5:00 a.m.Chicago O'Hare Intl

6h 18m

1 stop

YUL12:18 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 286

American Airlines

27 Mar

YYZ6:17 p.m.Toronto Pearson Intl

2h 00m

ORD7:17 p.m.Chicago O'Hare Intl

31 Mar

ORD7:23 a.m.Chicago O'Hare Intl

4h 37m

1 stop

YYZ1:00 p.m.Toronto Pearson Intl

C$ 298

Air Canada flights from Region of Ontario to Chicago

Our best Air Canada deals on Region of Ontario to Chicago flight tickets

Air Canada

19 Mar

YUL9:25 a.m.Montreal Pierre Elliott Trudeau Intl

2h 53m

ORD11:18 a.m.Chicago O'Hare Intl

23 Mar

ORD3:35 p.m.Chicago O'Hare Intl

2h 05m

YUL6:40 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 241

Air Canada

26 Mar

YUL9:25 a.m.Montreal Pierre Elliott Trudeau Intl

2h 53m

ORD11:18 a.m.Chicago O'Hare Intl

30 Mar

ORD8:40 a.m.Chicago O'Hare Intl

2h 11m

YUL11:51 a.m.Montreal Pierre Elliott Trudeau Intl

C$ 242

Air Canada

26 Mar

YUL1:10 p.m.Montreal Pierre Elliott Trudeau Intl

2h 45m

ORD2:55 p.m.Chicago O'Hare Intl

30 Mar

ORD8:40 a.m.Chicago O'Hare Intl

2h 11m

YUL11:51 a.m.Montreal Pierre Elliott Trudeau Intl

C$ 243

Fly from

Fly to

Route

Depart

Return

Price

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 19/3

6:50 a.m.-10:05 a.m.

1 stop4h 15m

Chicago Midway

Thu 26/3

11:00 a.m.-5:45 p.m.

1 stop5h 45m

C$ 228

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 28/4

6:50 a.m.-10:15 a.m.

1 stop4h 25m

Chicago Midway

Mon 4/5

10:25 a.m.-6:15 p.m.

1 stop6h 50m

C$ 230

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 19/3

9:25 a.m.-11:18 a.m.

Nonstop2h 53m

Chicago O'Hare Intl

Mon 23/3

3:35 p.m.-6:40 p.m.

Nonstop2h 05m

C$ 241

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 26/3

9:25 a.m.-11:18 a.m.

Nonstop2h 53m

Chicago O'Hare Intl

Mon 30/3

8:40 a.m.-11:51 a.m.

Nonstop2h 11m

C$ 242

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 19/3

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Thu 26/3

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 264

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Tue 17/3

6:00 a.m.-8:00 a.m.

Nonstop3h 00m

Chicago O'Hare Intl

Sun 22/3

6:00 a.m.-3:16 p.m.

1 stop8h 16m

C$ 265

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 4/4

11:00 a.m.-11:50 a.m.

Nonstop1h 50m

Chicago Midway

Sat 11/4

12:35 p.m.-3:17 p.m.

Nonstop1h 42m

C$ 267

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 4/4

8:50 a.m.-9:50 a.m.

Nonstop2h 00m

Chicago O'Hare Intl

Mon 6/4

9:20 p.m.-11:59 p.m.

Nonstop1h 39m

C$ 269

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 4/4

9:45 a.m.-11:37 a.m.

Nonstop2h 52m

Chicago O'Hare Intl

Mon 20/4

7:13 a.m.-10:40 a.m.

Nonstop2h 27m

C$ 271

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 10/4

7:00 a.m.-8:03 a.m.

Nonstop2h 03m

Chicago O'Hare Intl

Sun 12/4

8:45 a.m.-2:19 p.m.

1 stop4h 34m

C$ 274

Flights are sorted by cheapest round-trip flights first.

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How to get the cheapest flight ticket from Region of Ontario to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Chicago?

The month of June is another great option to travel to Chicago, with average flight prices from Region of Ontario averaging around C$ 304.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 577. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around C$ 999. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

In the morning is the cheapest time of day to fly from Region of Ontario to Chicago when you can find flight prices for as low as C$ 644. Flying to Chicago in the morning is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,104 per ticket.

What is the cheapest Ontario to Chicago flight route?

Fly from Toronto Pearson Intl to Chicago O'Hare Intl for the best Ontario - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Region of Ontario when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 394 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Region of Ontario for as low as C$ 267 on momondo.

What cabin class options are available on Ontario to Chicago flights?

There are 4 cabin classes available to choose from on Ontario to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Region of Ontario to Chicago flights?

No. A direct flight is the cheapest option for a flight between Region of Ontario to Chicago.

Cheap Region of Ontario to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Region of Ontario to Chicago

Best price found	C$ 270
Fastest flight time	1h 50m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Region of Ontario in the past 72 hours is C$ 270. The best round-trip flight deal from Region of Ontario to Chicago found on momondo in the last 72 hours is C$ 285.

The fastest flight from Region of Ontario to Chicago takes 1h 50m

Direct flights go from Region of Ontario to Chicago every day.

There are 3 airports in Chicago. From Region of Ontario there are direct flights to Chicago Midway (MDW).

Search flight deals

When did momondo last update prices for flights from Ontario to Chicago?
Prices for flights from Ontario to Chicago were last updated today.
How many operators does momondo search for flights from Ontario to Chicago?
There are 5 operators available for flights from Ontario to Chicago as of February 2026.
How old do you have to be to fly from Ontario to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Ontario to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Region of Ontario to Chicago?
Based on momondo bookings for flights between Region of Ontario and Chicago, the leading plane model is De Havilland (Bombardier) DHC-8-400 Dash 8Q, making up 14.63% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 13.20%, Embraer 195 E2 with 10.80%, and Embraer 170 with 9.53%.

Best airlines flying from Region of Ontario to Chicago

Compare and see reviews for airlines that fly from Region of Ontario to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Porter Airlines	PriceFrom C$ 112	Free Cancellation	Rating 8.0 419 reviews	Search Porter Airlines flights
American Airlines	PriceFrom C$ 222	Free Cancellation	Rating 7.2 11,338 reviews	Search American Airlines flights
Air Canada	PriceFrom C$ 245	Free Cancellation	Rating 7.1 10,738 reviews	Search Air Canada flights
United Airlines	PriceFrom C$ 259	Free Cancellation	Rating 7.4 9,341 reviews	Search United Airlines flights
WestJet	PriceFrom C$ 365	Free Cancellation	Rating 7.2 3,270 reviews	Search WestJet flights

Munster

Hammond

Merrillville

Why use momondo?

Why should I use momondo to find a flight deal from Ontario to Chicago?

Finding the right flight to Chicago from Ontario is quick and easy when you have a range of options in front of you, from reputable agents and recognizable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Ontario to Chicago with flexible booking policies on momondo?

Flights from Ontario to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Ontario to Chicago?

Once all potential Ontario to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Ontario to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Ontario and alert you when they change.

An easier way to manage your Chicago trip

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Cheap flights from Ontario to Chicago from C$ 157

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Ontario to Chicago departing on 19/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Filter for what you want

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American Airlines flights from Region of Ontario to Chicago

Our best American Airlines deals on Region of Ontario to Chicago flight tickets

Air Canada flights from Region of Ontario to Chicago

Our best Air Canada deals on Region of Ontario to Chicago flight tickets

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How to get the cheapest flight ticket from Region of Ontario to Chicago

What is the cheapest month to fly to Chicago?

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

What is the cheapest Ontario to Chicago flight route?

How far in advance should I book a flight to Chicago?

What cabin class options are available on Ontario to Chicago flights?

Can stopping save me money on Region of Ontario to Chicago flights?

What is the cheapest airline that flies from Ontario to Chicago?

Which airlines fly to Chicago?

How many flights depart from Region of Ontario to Chicago on average per day?

How many flights depart from Region of Ontario to Chicago on average per week?

How long does it take to fly to Chicago?

Cheap Region of Ontario to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Region of Ontario to Chicago

Best price found

Fastest flight time

Direct flights

Airports in Chicago

Best airlines flying from Region of Ontario to Chicago

Compare and see reviews for airlines that fly from Region of Ontario to Chicago with momondo

Travelling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Ontario to Chicago?

Can I find flights from Ontario to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Ontario to Chicago?

I’m not ready to book a flight from Ontario to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago

Fly your favourite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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